Seven-year-old Tahlese smiles while holding her instructor's arms nervously as she attempts to glide down a ramp on a skateboard for the first time.

After several attempts, the second grader at the Monarch School in downtown San Diego finally lands the trick.

"I did it!" she exclaims during a skateboarding session through the Encinitas-based nonprofit Rollin' from the Heart on Oct. 31 at the school. "Every time I go on a skateboard it makes me proud of myself that I did it, and it shows people that I can do it. I feel scared when I'm on the ramps because I might fall and hurt my head, but I have a helmet on and I won't fall."

The confidence Tahlese feels when on a skateboard is exactly what Encinitas couple John Barry and Alison Brown were aiming for when they created their nonprofit four years ago, following the passing of their son, Ian.

The couple founded Rollin' from the Heart one year after 22-year-old Ian “Poods” Barry fell off a bluff in Encinitas and died as a result of his injuries.

"When he passed, it was just overwhelming for us in terms of how many people he affected in his life," Brown said. "He was just a very shy, quiet kind of guy until you got to know him. He didn't think people remembered who he was when he was alive. When he passed, we had 500 or 600 people at his memorial."

More than 80 people have a tattoo honoring Ian. Locals refer to the new Encinitas Skate Plaza as “Poods Park.” And Rollin’ from the Heart aims to carry on Ian’s legacy of kindness and “less technology, more nature.”

Antonio Smith, 14, a sophomore at the Monarch School in San Diego, practices a kick-flip on a skateboard during a Rollin’ from the Heart session on Oct. 31. Brittany Woolsey

The nonprofit, which works with the Monarch School and two other organizations in San Marcos and Oceanside, offers skateboarding, surfing and other outdoor activities, through donations, along with classes about self-esteem, for disadvantaged youth in San Diego.

"One of the things that kept coming up about Ian was that he was this really kind, compassionate and accepting person," Barry said. "We wanted to add those attributes into things that kids would be attracted to."

The Monarch School, which the nonprofit began partnering with three years ago, works with children affected by homelessness. A representative from the school said Tahlese's family is currently living in housing provided by the school.

This is the first year Rollin' from the Heart has been added to the school's curriculum. The nonprofit has also donated clothing and meals to the school.

Katie Bradel, director of development at the Monarch School, said Barry has become a mentor to the students.

"A huge goal for everything we do here at Monarch School is to support our students' motivations into making sure they realize that they matter," Bradel said. "Every single student has a different interest and motivators. Skateboarding is definitely a huge motivator. Students from age 5 to 18 feel confidence when they learn a new trick or go skateboarding for the first time, and that trickles down to all areas of life: academics, self-confidence and relationships."

Antonio Smith, a sophomore at the Monarch School, who skateboards regularly, said Rollin' from the Heart has helped him connect with others.

"It's helped me with understanding how to be social with people and how other people's feelings are," the 14-year-old said during the Oct. 31 Rollin' from the Heart class as he practiced a kick-flip at the school’s portable skatepark, set up by the nonprofit. "I get to have a social bond with people because we're all skateboarding together."

While Barry said he would like to see Rollin' from the Heart expand someday, it's important to focus on San Diego for the next few years.

Ideally, he'd like the program to reach more than a dozen schools and organizations in the county.

"We could spend the next three years in San Diego and still not reach all the kids we want to reach," he said.

The nonprofit is also looking to expand its surfing program. In order to do so, Barry is looking to raise funds for a vehicle to take students to the beach.

Fundraising is vital to help the nonprofit thrive and support its programs, Barry said, adding the group is comprised mostly of volunteers.

"We don't want to over-extend ourselves, over-commit and under-deliver, so we want to be very careful about how we grow to make sure that we can do a good job with those who we work with," he said.

Those interested in donating to Rollin' from the Heart and learning more about the nonprofit should visit rollinfromtheheart.org.